Water → HCID 54521452, compound

HRID 745360Notes

Reaction equation

HRID 745360 reaction equation
[CH2:1]([SH:4])[CH:2]=[CH2:3].[CH:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[N:19][O:20][CH2:21][CH2:22]Br)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:12]=1)=[O:6].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([S:4][CH2:22][CH2:21][O:20][N:19]=[C:13]([C:11]1[N:12]=[C:8]([NH:7][CH:5]=[O:6])[S:9][CH:10]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13367Allyl MercaptanHCID 53939076HCID 53939076, compound

Product 1

HCID 54521452HCID 54521452, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Allyl mercaptan (2.12 g.) was added dropwise to a stirred suspension of ethyl 2-(2-formamidothiazol-4-yl)-2-(2-bromoethoxyimino)acetate (syn isomer, 5 g.) and potassium carbonate (3.95 g.) in N,N dimethylformamide (50 ml.) under ice cooling and stirred at the same temperature for 10 minutes and further at room temperature for 5 hours. After adding water (300 ml.) to the resultant solution, the mixture was extracted with ethyl acetate three times. The extracts were washed twice with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The oily residue was subjected to column chromatography on silica gel and eluted with chloroform. The eluate was concentrated in vacuo to give ethyl 2-(2-allylthioethoxyimino)-2-(2-formamidothiazol-4-yl)acetate (syn isomer, 4.0 g.), mp. 62° to 64° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. washThe extracts were washed twice with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. washeluted with chloroform
  6. concentrationThe eluate was concentrated in vacuo

Sources & evidence

ORD record
ord-61c44ea7e60041fb88a5d059c271d82b
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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